


Hell over Heels

by RainiDayz



Category: Supernatural
Genre: Chaptered, Crobby - Freeform, Crowley Has Feelings, Heaven, Hell, M/M, Short Chapters, Slow Build, arguing like an old drunken couple, could be canon?, dont piss off crowley
Language: English
Status: In-Progress
Published: 2014-12-02
Updated: 2014-12-09
Packaged: 2018-02-27 20:30:49
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 13
Words: 11,720
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2705768
Author URL: https://archiveofourown.org/users/RainiDayz/pseuds/RainiDayz
Summary: <blockquote class="userstuff">
              <p>"Nice try. I know my bones were torched when I died and I didn't go with any reaper."</p><p>"Yes, but reapers don't always have to give you a choice, now do they? Not if you pay them right."</p>
            </blockquote>





	1. A Royal Welcome

Bobby could only smile sadly as the flames began to wash over his flask, severing his only bond to earth and his boys. He felt the flames fanning about his feet and made sure he didn't scream out when they watched him depart. This was it. His hunter's funeral and his big, last hoorah. He closed his eyes, waiting for darkness, and to finally be at peace.

"Hello Singer."

His eyes snapped open, taking in his surrounding as he realized he was at home, sitting on his old couch surrounded by dusty books of lore and odd spell items. This wasn't right. He tried to stand, but found himself stuck in place by an unpleasant force he recognized almost instantly. He heard a chuckle and turned slowly to see not surprisingly where it had came. There, leaning casually, drinking scotch in the kitchen doorway, was Crowley.

"... _Balls_." Bobby hissed venomously, not taking his eyes off the demon as he walked in front of him with a grin.

"Missed you too, Darling." The King of Hell purred, "Been a bit of a drag with just the boys, seeing as their hands have been full of Dick, wouldn't you say?" Bobby didn't reply, but merely focused his energy as he had learned as a ghost to move himself from the sofa. " _Ah-ha ha_ ," Crowley tsked, wagging a finger at him and reapplying the pressure. "Can't do that here. You're not just floating around in space anymore, you're in my home."

"Really? I'm in Hell?" The hunter rolled sarcastically. "Nice try. I know my bones were torched when I died and I didn't go with any reaper. And I just watched Dean incinerate my flask."

"Yes, but reapers don't always have to give you a choice, now do they? Not if you pay them right."

Bobby gazed up, locking eyes with the demon. "What are you sayin'?"

"I'm saying that this is your grand stop. Your, final destination. I'm guessing the boys would be surprised, wouldn't you?" With a snap, Bobby settled more easily into the couch and most of the tension was gone from his body. "Feel free to carry on whatever it is you do. Oh, an if you need Winchesters to play with, I can provide that too." He snapped again, and an astonished Dean and Sam appeared in the doorway, confused and relieved.

"Bobby?" Sam questioned, becoming misty eyed as Bobby turned back to the demon fuming with rage.  


"Why you sorry son of a-"

"Ah ha, now is that anyway to thank me? I could have you tortured for killing off plenty of my men."

Bobby opened his mouth, but something in him shut it promptly and all he could do was glare.

"Good boy." Crowley grinned and vanished without another word.


	2. Team Free Will #2

Bobby wasn't sure how long he had been in Hell, all he knew is that it was, well... Hell. He was trapped in a day that never ended and though he was tired, he was never able to sleep. Every now and then a demon or two would show up and try to encourage or provoke him, smiling the devilish grins of the Winchesters with soulless black eyes. He tried to fight them, using everything in his personal home arsenal that he knew how, but they weren't _his_ ingredients, and they weren't _his_ spell and lore books. They were _**Crowley's.**_ And nothing in them could rid him of the awful visage of his boys. He had to hand it to the demon. Every detail was downright flawless, right down to the dusty cracks in the kitchen tile or the creek of that one wooden floor board. It was like living in a nightmare that he never would have thought possible and defiantly didn't believe could be his perfect form of Hell. But anytime he started to settle slightly, maybe even becoming a bit comfortable as he adjusted to his surroundings, the King of Hell would swing by and remind him ' _there's no place like home, wouldn't you agree?_ '

"Oh come on, Robert, lighten up." The said demon scoffed as he splayed himself leisurely on the sofa. "It could be worse. You could be bunk mates with Juliet."

Bobby shivered at the reminder of the hell hound. He muttered _"Slobbering Mutt"_ before Crowley shot him as a glare as a warning. Fixation or no fixation, (whether he admitted to it or not), no one made ill comments about his favorite hound.  


"Remember who you're speaking to." He snapped and a glass of fine butterscotch whisky appeared in his hand.  


"Oh yeah, and what if I don't?" Bobby turned from his standing, challenging him. "You gonna torture me? You do it enough already with the boys so if you can do any worse than that, I'd like to see ya try."  


"Oo, my neathers tremble when you get all heated like that." Crowley purred with a smirk, letting slip the bitter _"Idgit"_ from the other. "You know, I never would have expected you to be this easy. I figured I'd have to have my men on watch for you by now."  


"Why's that? Cause ya think I'll try runnin' outta Hell?"  


"Don't see why not."  


The hunter narrowed his eyes in suspicion at the demon. "And where, prey-tell, would I go?"  


Crowley shrugged. "I don't know. 'Round the back, loop through Purgatory, over the moon, and into heaven, I suppose?"  


"'Cause when ya put it like that, it's that simple isn't it?" Bobby sighed and sat back in the old chair behind his desk, rubbing his hands over his face in restless irritation. The King of Hell then stood and and approached him, leering over the desk.  


"You shouldn't fret so much. Who knows, you may start to enjoy your stay with me. Perhaps, even..." He leaned over the scattered documents and papers and captured Bobby's attention as he whispered by his ear. "We could have some fun striking a deal."  


"A deal, huh? Like the last one?" The hunter scoffed as the demon moved back behind the desk. "Hell no. Ya already have my damn soul, what else could ya want?"  


"I'm sure I could think of a few things if I really tried." Crowley gave him a once over with a Cheshire-like grin then turned away. "I have some business to attend to at the moment, but do let me know if you change your mind."  


"Why don't you ask one of your little deal-breakers to beat it out of me?"  


"Oo, there it is again, that ornery derision." He perked up and turned to the drunkard once more. "They would ruin the whole thing. Free will is the only way to make things interesting with you."  


"And bein' stuck down here with Dumb and Dumber is free will?"  


"More than you know, Darling." He retorted, leaving with a hollow snap and leaving Bobby to revel in the re-pungency of his freedom.


	3. Deal?

At one point in his nightmare, Bobby had tried to keep track of time. He grumbled about it all the while as there was no way of telling of what he was doing was accurate or if time was even creeping at all. For all he knew, Crowley could freeze his time; he'd live through an eternity down here before Dean even finished his burger up on the main floor. Not to mention the demon Winchesters that came to bug him becoming more and more instistent, simply for the purpose of causing him unwanted stress and miscontent. One day was particularly a point of heat to him. 

"So Bobby," Dean sighed, plopping himself on the couch and slipping idly through a book on rugaru's. "Tell us again how Karen died." 

The hunter froze, wrath jolting into his system as he clenched his fists into tight balls and ground his teeth together. 

"You know how," He growled menacingly, eyes burning beneath the brim of his hat, but having no effect on the Deanmon. 

"Yeah I know, but you guys got into that huge fight before she got possessed." He glanced up, sitting forward and meeting the hunter's vehement gaze. "Are you sure you didn't want to stab her _before_ that happened?" 

There was a swing, an impact, and and explosion. Almost instantaneously the mouthy demon was nothing but scattered blood stains and Bobby was filthy. He blinked in confusion and turned to find Crowley facing away from him and towards a very alarmed looking Sammy. 

"I gave you the specific order not to ruin him, did I not!?" The Kind of Hell boomed, the room nearly shaking in his anger. 

"Yes, sir, I'm so sorry, but it wasn't me, you saw it was Keith! Ipromiseitwon'thappenagain, please-" 

There was another explosion and splatter, the moose now a red mousse on the carpet. Crowley turned to face Bobby, muttering to himself as he pulled a red handkerchief from his jacket and wiped the blood off his face. The demon looked up to see the other's face full of both confusion and awe. 

"What?" He spat quickly, wiping finally around his jaw then stuffing the offending article back into his pocket. 

"I dunno, you tell me considerin' you just blasted two of your guys into purgatory." Bobby retorted, not taking his eyes of the other as he came closer. 

"Oh God, you're filthy don't come near me." Crowley made a face of disgust and snapped, cleaning the demonic bio-hazard away from them all. "Any how, I could see they were taking things a tad too far, so I intervened." 

"A _tad?_ " The hunter snorted. 

"A lot." The demon corrected. "Either way I fixed it, yes?" 

"Yeah," Bobby furrowed his brows and focused in on the creature, trying impossibly to figure him out. "I'm just wondering why you _did_ fix it." 

Crowley's features contorted slightly, as if he was misunderstanding the question. "Why wouldn't I?" 

"Gee, I dunno cause they're your demons and I'm in Hell?" 

The King rolled his eyes and turned with an annoyed sigh. "You really are simple aren't you?" He asked with a curl of his lip. "I could have you in far worse scenarios if I wanted, as you seem to frequently forget. There's a reason I have you in Hell." 

"That's what I'm afraid of." The hunter recoiled, eyes still scanning over the demon. 

Crowley waited for a moment then made a short clicking sound with his tongue. "Tell you what," He offered. "You stop you're quote-unquote bitching, about being stuck in Hell, and you won't have to bother with anymore Winchesters. Deal?" 

The hunter wasn't quite sure what to make of the deal, but God did it sound good. He couldn't stand seeing demons running around in faux Dean-and-Sam meat suits. It was killing him more than being trapped with Crowley was. 

"'Sounds like a hell of an offer." 

"That's what an Ex-Crossroads King is best at." Said King smirked and stepped up to Bobby, just enough to get him close and make the other feel slightly uncomfortable. "So, have we got a deal?" 

Bobby scowled and growled slightly before dodging down and capturing the demon's lips with this own. This time he stood over him slightly and took hold of his arms, gripping them tightly and keeping them in place. He'd be damned if he let the bastard get another picture. Well, more damned... 

Crowley's smirk increased with the added contact as he forced himself up against the hunter's body, being slowed only slightly by the hold of his arms. He kissed the other back with the same force, blunt and not really meant to be enjoyable, but enough to make him content and his deal worth while. 

He slid his lips a tad lower and took hold of the hunter's lower lip in his teeth, biting it harshly, but not enough to draw blood. Bobby responded with a hiss and forced his mouth back over the demon's, pushing it open and taking full control. Memories from selling his soul flooded into his mind and only pressed him further. Crowley didn't mind at all, honestly. He could let the hunter take control over him this time simply because he prodded him. In his mind, Bobby was actually quiet the kisser and he could swear (though not admit) he could feel himself being slight swept off his feet. 

When the hunter was satisfied he didn't shove Crowley away but rather forced himself back, both of them flushed and panting madly as he glared at nothing in particular. 

"Well Robert," Crowley said at last, running a hand over his mouth as if to soothe it. "I must say you drive a bargain for a smooch like that." Bobby didn't respond. "Enjoy your solitude. I'll be in later. Ta." 

He vanished into the air once more, leaving Bobby in accented silence and a ferocious tingling in his lips he wouldn't soon forget.


	4. Hiya Sammy

Crowley kept his solemn word, unlike Bobby had expected. Not once since their kiss of accordance had he seen a Winchester. It made him depressingly euphoric. He never seemed to find himself lonely for too long though. The King of Hell would visit him often in his rounds, like clockwork he would presume if he had known the time. In his isolation, he had started to become accustom to the odder traits of the demon; his scent of smoke and whiskey surprisingly lacked pungency of sulfur, the various grins and smirks that indicated the varying degrees of his mood, and his almost unconscious necessity to have him in close range. If ever he moved into another room, it wasn't long before he was followed, and while sitting on the couch, Crowley would rather take up the seat beside him rather than one in the multitude of open chairs. In a way it almost reminded him of Castiel, though not so intercepting his personal space and more understanding every notion of pop culture, some of which he himself sometimes didn't catch. 

What surprised him the most, however, about all of the visits he received, Crowley seemed more than eager to grant him any wish he so desired. He had mentioned once that he had wanted to be able to sleep (though he didn't need it physically, he was mentally exhausted.) and the demon offered to make it so. When it came to the fee, Bobby had absolutely nothing to give, so instead he laid the offer on the hunter himself. 

"Another proper snogging will due, I suppose." He had engaged with a smirk, waiting for the next move. 

After a moment Bobby found himself complying and once again dominating the King's lips with his own. These small deals became more and more frequent, to the point where even in a quiet paradise the hunter would find himself locked onto the demon by the end of each of his trips. They also had become increasingly more physical. Where Crowley's arms were once held in place, Bobby's hands always seemed to travel down to narrow hips and occasionally the small of the demon's back. Crowley to would sometimes manage to snake his arms over the other's shoulders and find himself gripping the blades or the back of his neck, and he kept himself pressed tight against the other. These little habits became just a part of the natural order over time, and slowly Bobby stopped hating himself for it and actually started looking forward to the demon's visits. Where it had once been tension and sarcasm was now a mix of swapping opinions and stories as well as satire and jokes between them. Living in Hell was starting to grow on him in a way, that is until it all stopped. 

One day Crowley didn't come, and Bobby felt the soft pang of sorrow at the loss of his demon. The next day the King was no where to be found, and the day after that the same. Misery had started to completely over whelm him until finally, his world shattered. Instead of his bed, he woke up in a damp, dark room; stone walls scratched with tallies and writing he'd never seen. He was about to call for Crowley and ask what in the name of Hell was going on _in_ Hell, but before he could, he noticed a visitor. In his doorway, in a flannel shirt and jeans, _"moose locks and all"_ as Crowley would say, was Sam. 

"Bobby?" He asked shakily, a smile playing on his lips. 

The older hunter remained wordlessly stunned for a moment as a smile came across his lips. _"Sam?"_

The Winchester quickly clamped him in a tight hug, patting at his back before asking "How've you been holding up?" 

"How have I _been_?" Bobby pulled away and looked at him as if he had three heads. Though his nightmare had only just become, he replied. "I've been in Hell, what do you think?" 

"Yeah, that's true." Sam, half chuckled. "But then again you deserve to be down here don't you?" 

The elder froze, stunned by the bluntness and the tone. "...What?" 

He watched as Sam's lip curled into a smirk and those warm, misty eyes clicked black. "After all, you _did_ kill your wife, remember?"


	5. Wait, Sam?

Bobby wasn't sure how many Winchesters he had gone through, nor how long he had been struggling inside his new cell. He didn't know if Crowley could hear him calling or if he was behind it all. Could he be behind this? Building him up in an afterlife too good to be true only to have everything stripped away from him, to slowly gain his trust only to find out how to ruin him? The thought itself infuriated him. He knew he shouldn't have let himself get caught up in making deals with the new devil. He knew he should've stuck to his gut and focused on a way to get out of Hell, rather than make it 'Home Sweet Hell'. He knew he never should've allowed Crowley to get close to him, never allowed himself to begin fancying his little quirks and grins, sarcasm lacing almost every phrase or the hum in his voice when he sang even when it was meant to mock him. That, is truly what had hurt, he believed. Every gesture and kindness Crowley had expressed only to him had been pure snake oil. Faking everything; every act and kiss and emotion was a con. It was killing him inside. 

While he was stewing in his anger and heartache, he heard soft footsteps and the lightest creak of his door opening. He had gotten so used to the intrusion of his space and thoughts, he made no effort to turn when he heard another one of the indignant demons enter his room. 

"Bobby?" This one, clearly voiced as the younger Winchester, called out, stepping closer behind him. 

Carefully the hunter turned and met his gaze. This one looked surprised, worried, and confused, his brows knitted together just a touch and lips were parted slightly, as if analyzing the situation. He looked just like the real Sam would. His hatred reached a boiling peak. Swinging fast, he stuck the demon in the face full force and felt the heavy impact in his hand. The Winchester stumbled back and fell with a grunt. 

"Get the hell out of here, you black eyed son of a bitch." He hissed, ready to swing again if he needed another reason. 

" _What?!_ " The demon stood and gawked at him in an exasperated fashion. "Bobby, it's Sam!" 

"Yeah, and I'm Elvis. Move your ass!" The hunter growled more furiously this time, not being fooled by the fake-Sam's act. 

"Bobby-" 

"Get!" 

" _ **IT'S ME!**_ Okay," Sam took a breath to calm himself and continued."Okay, _dammit_ , if it's not Sam, then how do I know about you and Tori Spelling?" 

Bobby squinted his eyes at the demon and tried to process what he said. " _What?_ " 

"You're a fan, yeah." Sam nodded, focusing on him intently. "Or... or, uh, okay. What about your free pedicure at the Mall of America? You made Dean swear to never tell another living soul how it changed your life." He said matter-of-factly, pointing a bizarre sword and nodding in conclusion. 

Bobby stared at him agape for a moment, not having the sheer hope to believe what he was hearing. " _Sam?_ " He tested carefully, as if whispering would make it easier. 

Sam sighed and chuckled slightly with a nod. The hunter lunged forward and captured his boy in a tight hug, not sure how and not really caring, but damn more than ecstatic to see Sam. The _**real**_ Sam. 

"I'm sorry Sam," Bobby sighed, the name itself felt almost foreign on his lips. "But you're the _200th_ Sam I've seen today. That's how they screw with me." He grumbled, once again remembering Crowley and the first deal they had made. He knew the once King of the Crossroads almost never went back on a deal, but he had done it before when his soul was on earth. It hurt and it reminded him of the first time he had seen his boys in Hell. "Just endless Sams and Deans all wearing the same black eyes. -Wait a minute." Realization stuck him. "What the Hell are you doin' here? Please don't tell me it's what I think it is..." 

Sam's eyes widened and he shook his head. "No, no, no, Bobby, I'm good, I..." He sighed. "I'm here to get you. You don't belong here Bobby, and we're getting you out." 

He passed over the demon blade to the other hunter who took it in silence. What he wouldn't give to find Crowley and make him feel what he felt right now.


	6. Bureaucrat Bitch

Escaping Hell itself was far too easy in Bobby's mind, and the trek through purgatory uncovered that since his death his boys had completely derailed, but he still had faith in the both of them. Once Sam was through the portal and met up the Dean, Bobby was more than ready to be released from earth, even if he may never come back. Sam said the spell and he felt light as air, ascending gracefully until he was suddenly stopped, swallowed up by black smoke. Then he heard it. 

" _Hello, Boys._ " 

Crowley. That _**damned Crowley**_ had stopped him, and now he was absolutely defenseless. Why couldn't he be in his humanly vessel and shove the demon blade up the King's ass? 

"Bobby Singer," The demon looked up to him, smiling smally (though unusually forced, he noticed) as he held him in place. "I'd know you anywhere." The hunter could not respond, but only shift furiously in the clouds above. 

"Let him go, Crowley." Dean demanded bitterly. "He doesn't belong in hell." 

"He does if I say he does." Crowley hissed back, his tone dark and more than angered. "He's inflicted untold damage on my kind. From where I sit, actually, Hell's too good for him." The Winchesters stepped forward and he lifted a hand, flinging them back against the trees and keeping them hung. " _Really?_ " He grinned to himself than up to Bobby, still shifting restlessly. His soul began descending back to Hell when again, he was stopped. "What?" He turned and noticed the angle before him, smiling sweetly and unwavering. "Oh, come on!" 

"Let me see if I've interpreted the situation correctly." She started, speaking in her all too know-it-all, formal tone. "The Winchesters have feed an innocent from Hell, to which you are wrongfully trying to return it." 

"Sliding with them, Naomi?" Crowley shot back. "You don't know those two. Before they're done, we'll both be locked away." He knew this to be true. The Winchesters, though destructive, reckless, and dependent, always got what they set out for. If he couldn't find a way to hold some leverage over them fast, he knew Hell would locked shut. He'd be stuck once more with nothing but demons, dirty human souls, and endless screams. He couldn't allow for his paradise to be destroyed. And he couldn't allow Bobby to go into Heaven, not if it locked him there too. He wasn't willing to give up his hunter. 

"I'm just hoping they lock _you_ away, dear." Naomi smiled. "The rest, I'll figure out." 

"Bureaucrat!" The demon spat in disdain. "You're fighting outside your weight class." 

" **Don't** call me a bureaucrat." Naomi straightened, taking him on, unwilling to stand down. She began to glow and raise her hand. 

Crowley thought quickly about his options. He either needed to get away now or be smited by a political-asshat of an angel. If _only_ he had brought an angel blade, he would be able to stop her. He swallowed hard, taking down his pride and swore to himself he wasn't going to let those two numb skulled Winchesters slam the gates of Hell on him without Bobby. Nor let them shut the pearly gates of heaven closed on the hunter. He scowled and made his choice. 

Before Naomi could strike, he vanished.


	7. The Desolation of Crowley

The King of Hell skulked in his room, twitching in agitation as he tried to come up with a way to get back at the Winchesters. How dare they steal from him, the thought alone made him want to snap their necks and lock the in the pit with Michael and Lucifer. Fury boiled inside him as he paced, stomping endlessly as he kept losing his focus. If it were any other situation, he would have a plan by now. He would know exactly who to cast for the handy men and how to execute it, but his ideas kept being veered off course by the thought of Bobby. 

When he had felt the other man's soul, trying not to let it escape him, he felt all the wrath, betrayal, and anguish it contained; all of which he knew was his fault. But it _wasn't_ his fault. It was those bloody Winchesters. If they had just kept things in the natural order, demons and angels free to roam around as they liked, than none of this would have happened. He wouldn't have had to leave Hell. 

Being the King of Hell, he could control everything; torture, demons, hell hounds, the environment. But the moment he left, it returned to an almost factory setting. All souls in Hell were either locked away or destroyed some how, and the demons often felt no need to follow orders but rather to do what they were designed to, most of which being to torture the souls. 

Crowley hadn't intended to leave Bobby the way he did, truthfully he did all he could to avoid it. But those damned Winchesters were getting out of hand, and dealing with the prophet was another story entirely. He was practically forced to make a move and leave Hell, leaving Bobby to suffer without having any knowledge of why. 

The demon growled at himself. For the love of all things unholy, he knew he enjoyed fooling around but he didn't think he was able to _care_ this much. Caring was supposed to be a _human_ thing, like emotions. He hadn't felt an ounce of emotion for humanity before now, and damn was it going to kill him. It was severely pissing him off. _Robert Singer?_ _**Honestly?**_ An ornery old drunkard from Sioux Falls, and a hunter no less? Was he honestly this _naive_? 

He should be pissed at the fact the Winchesters stole something from him, not that the thing they stole was Bobby. When had he grown such an affection for the man? He was a _demon_ for God's sake, he wasn't suppose to feel anything but hate for anyone! But somehow through the whiskey and derision, he had actually begun to fall for the hunter. So much so now, he wasn't entirely angry with his situation, he was _devastated_. 

Eventually the pacing stopped and he let himself fall back into his arm chair with an exhausted sigh, rubbing his hands over his face. There was a whine from the corned of the room, and Juliet stood and trotted over to her master, laying her big slobbery head in his lap. 

"Get off me, mutt." Crowley shoved her off. 

Again there came a whine but she obeyed, sitting up still beside the King in his throne. Crowley looked to her and sighed. He could never be mad at her, and honestly he was relieved she wasn't the Winchester's victory in the first trial. 

"Come here." She padded around in front of him and he petted her affectionately for a moment, patting her in content before he sunk back into his chair once more. Another trait of humanly emotion had peaked through. He swiped his hands over his face once more before returning to his thoughts on how to get revenge on the boys, memories of Bobby continuing to rot his demonic foundation. 

"Bollocks."


	8. Deal of a Lifetime

It didn't take Crowley too long after his realization to come up with a more than suitable plan for the Winchesters. All it took was a little bit of scouting, a touch of reading, and before long he could have them both at his feet. When played the plan rolled along as expected; he killed a couple ex-victims, the boys caught on and inevitably saw one of them die, he held the poor little sheriff from Sioux captive, and Boom. Winchesters on a platter. 

"What's that old expression?" He had asked, grinning as the hunters greeting him in scowl. "Success has many fathers, failure is a Winchester?" 

He remained pleased with himself as he unrolled the contract, watching the boy squander over it and oh, how he enjoyed it. Screwing them over in the most monumental way to them, the same way they had done to him. The squirrel murmured as he read up the contract, ignoring the demon's commentary and speech on humanity up until he was finished and the page was ready for signing. The moose gave a light nod and Crowley was suddenly cuffed to Dean. He looked to each of the and furrowed his brows together. 

"Is this a _joke?_ " Receiving no answer, he shook his head and let the contract fall to the ground in disbelief and annoyance. "You realize all I have to do is-" He snapped. 

" _Unh unh unh_ ," Dean grinned. Crowley paused. The Winchesters were still in front of him. " _Demonic_ handcuffs, jackass." The demon stared at the device in confusion and noticed all the horrid symbols etched on the sides. "No flicking, no telephoning, no smoking out. Oh, and no deal. Which pretty much means that you're our bitch." 

Crowley was instantly heated. "Fine." He spat with interest. "You want to play chain-gang? _Lets._ " He pulled back his free fist and struck at the elder Winchester as hard as he humanly could, causing him to stumble back. "You saddled yourself to the wrong bull, mate." 

He was stopped by a harder fist flying back into his face, causing him to let out a pained grunt drawing blood from the side of his mouth. In his stun, Dean pulled out the angel tablet and passed it to Sam, then straightened him up by the collar. 

"I could do this all day, 'cause you know what?" He smiled, beaming at the demon before him. " _Damn_ , it feels good!" Crowley negated his focus from the squirrel to the cut in this lip, tasting heavily of iron and sulfur. Dean continued "But sooner or later, you're gonna have to face it- your ours. Which means your demon ass is going to be a _mortal_ ass pretty damn quick." The demon stopped. 

Crowley shot an uneasy look to Sam, both wanting to and not to know what the other Winchester was saying. "What's he mouthing on about?" 

" _You're_ the third trial, Crowley." 

The demon's world froze around him. _He_ was the last trial and the Winchesters already had him. He was going to become mortal. If he could have had the thought to process it, he would have noticed another human emotion coursing through him for the first time - _**Fear**_.


	9. A Guardian Hunter

When Bobby opened his eyes, he instantly realized where he had been sent. He was in his home, surrounded by spell and lore books, rare ingredients, and laying on the couch as if he had been taking a nap. He sat up carefully, eyes narrowing and searching for any visible signs of sulfur or demonic evidence. Finding none, he wandered through the rooms, trying to take in his predicament. Was _this_ his heaven? 

"Seems a little dull..." He muttered to thin air. No response. No movement. He was utterly alone. 

_This_ was the after life people sought after? To be permanently set in one place _alone_ for all eternity? _What kind of paradise was that?_

Though Bobby never had a real family, he had Karen while she was alive, then came in contact with more hunters than he could count, and eventually met John and his boys. They were the ones he had last been with. Well, while he was alive. 

Images of Crowley began to sink into his mind and he was instantly disgruntled. How had he allowed himself to get so weak, to be tricked into thinking that there might have actually been something between them? Crowley was a demon, he's the King of Hell for Christ's sake! The bastard had used him to find his flaws and work at them. He had used the excuse of deals to get close to him, to make him _happy_ to be stuck in Hell. He had used the length of time they were together to get the hunter to notice how adorning the demon's laughter could be. Not a snarky, arrogant chuckle like he usually pulled, but a full-bodied laugh that came only from the return of his own sardonic comment. And he had managed to use his body to draw Bobby unconsciously nearer; the way he stood, walked, even the way he sat on the couch could get the hunter to notice something. What had been just fooling around with sealing deals with kisses had turned into brushing elbows as Crowley watch him idly reading a lore book and the tilt of a head to rest on his shoulder while he was sitting at the desk. Bobby knew, he _knew_ and he could have _**swore**_ that given the opportunity, Crowley would be more that happy to be endlessly cuddled to death. And Bobby would have been quite alright being the one with him at the time. But then things changed. 

What the _hell_ had happened to Hell? And why couldn't he have reached Crowley? Why was he so devastated by the fact that he had been betrayed by a demon? It shouldn't have been a shock to him, it wasn't even the first time Crowley had done it. But still now it hurt, more than he could have ever expected; since he had seen the first demon Sam had come into his cell his chest felt tight and he felt like all the wind had been knocked out of him. All he could to think to ask was _**Why?**_

Bobby was brought back into reality by a light rustle coming from his kitchen. A spark of confusion and hope flared in him and he walked over to the doorway as quickly as he could quietly. He came around the corner and instantly froze. 

"Oh, hey Bobby." A man at his table greeted him. He had a sandwich and a beer in front of him, feet propped up on the table, and humming a tune as he ate as if it were the most normal thing in the world. 

" _Ash?_ " Bobby looked the mulleted hillbilly hunter up and down, not believing the sight. "What the hell are you doing here?" 

Ash swung his feet down to the floor to face more towards Bobby as he took a swig of the beer. "Well I was out doin' a little scoutin' about when I felt something familiar. I bobbed through a few doors, saw the heaven of a man you never want to meet, and now I'm here." He took another hefty bite of his sandwich before continuing. "How've you been holdin' up?" 

Bobby had to think about his answer. In all honesty he was miserable beyond belief, but he couldn't just say it was because some cheeky, smart ass demon had gotten the better of him. "Well, I've been..." He paused. He was bad. He couldn't be in heaven. He didn't want to be in heaven. All he ever thought was he was gonna be snuffed out like a light after he was burned. That all was nothing to him now. He knew what he wanted to do, even if he wasn't sure why. Either because he had grown too attached to the demon and wanted to know why he'd betrayed him or because he wanted to shove the demon blade where the sun didn't shine, Bobby wanted to find Crowley. 

"Bad." He finally answered. "I don't belong here, Ash." 

"What do ya mean?" The blonde questioned, tilting his head slightly. 

"I mean there's something I got to do, and I can't be up here on cloud nine to do it." Ash continued to stare at him boggled. Bobby rolled his eyes and continued. "I got to get out of here. Now, you mentioned you've been going through some kind of door?" 

"Yeah, the doors to people's heavens." The traveler explained. "Most people can't do it, but I've come up with a few tricks to go from nirvana to nirvana without getting caught by douche-wings." 

"Are there any doors _out_ of heaven?" 

"Only one that I know of..." Ash leaned forward, resting his elbows on his knees and fixed his gaze solemnly on Bobby. "The door to Purgatory." The older hunter's tongue caught in his throat. Purgatory. He was going to fight his way back through Purgatory to get to Hell. Was that even worth the thought? He would leave God's envision of paradise to go from the fire and back into the frying pan? The obvious choice was self evident, but Bobby just couldn't perceive it. He was so miserable, so upset, so _heartbroken_ , he couldn't just sit up in the sky forever. He needed to get to Crowley. 

"Well then..." He looked back to Ash, swallowing hard. "Guess you better show me where this door is."


	10. Confess to Impress

How had this happened to him? How had he, ex-King of the Crossroads, King of **Hell** , allowed himself to be captured by the Winchesters, dragged into a bloody church, chained further and shackled down to the floor like a dog? He fought against the binds, trying harshly to pull out of them as the older of the hunters finished the devil's trap around him. 

"You really think this is gonna hold me?" He asked, unable to glare he kept his eyes fixed elsewhere as he kept his tone calm. "That you're gonna cure me or whatever it is?" 

The squirrel didn't respond, merely shot him a look and tossed the spray can back into the church and headed out to meet with the younger, leaving him to continue his struggle. 

_How had this happened?_ How had he been brought so low? He couldn't be here for this. He couldn't let them turn him mortal, not even risk it. The moose walked in a moment later, heading into the empty, broken confessional. He was _cleansing_ himself. Crowley never understood that concept. After all the deception, the lies, the control and manipulation, the _killing_ , how could one even try to receive forgiveness? Who's going to forgive you, after all you've done? If he was looking for God, why was the ' _Holy Father of All_ ' going to forgive him, after slaying a countless number his angels and throwing Michael in the pit? What was he going to do now? Make promises he couldn't keep, and try to _impress_ him? 

After a few beats Sam emerged with an exhale, rubbing a hand over his face. He strolled by the demon and out the door without saying a word. Crowley wrung his hands in the cuffs, he wanted to growl or sigh, but at this point he could do neither. If he couldn't think of anything fast, this was going to be the end of him; his power, his ability, his leverage. As a demon he still had the hope he could somehow find a way to retrieve Bobby from heaven, but at as a _human_ he would have no chance at all. 

How must Bobby have felt when he left Hell? Crowley had honestly tried to keep the illusion up, to keep the other demons off of him and prevent the natural order of torment and trauma. For awhile he thought it was working, but the absolute fury and betrayal he felt radiating off his spirit said otherwise. The hunter probably thought he had done it on purpose. Crowley would never be able to forgive himself for that. 

He was brought back by the sound of the church door swinging open, the moose entering and moving to the table of supplies they had set up. The demon watched carefully as he stuck a syringe into his arm, retracting some of the blood. _Purified Blood_. 

Crowley swallowed hard and tried to keep up a dismissive tone. "You really think injecting me with human blood is going to make me human?" As the Winchester approached he ground his teeth together and spat "Did you read that on the back of a cereal box?" 

With a quick jerk his head was forced to one side, held in place as a slight gasp left his lips. Sam jabbed the needle into his neck and he let out a shout of pain. When he pulled back, Crowley whipped his head forward, growling at him. A moment passed, the hunter looking unsure of his method the demon chuckled darkly. 

"You're miles out of your league, moose." He whispered gruffly, Sam turned away. "See you in an hour." 

For a moment, Crowley felt almost relaxed, happy to see the brothers had once again fallen on their faces, but he was stopped when Sam groaned in pain and his arms started to glow within the veins. Fear returned to the demon and his eyes widened slightly, running a tongue over his lips in a rushed attempt to think. He was in trouble.


	11. Forgive me Sam, for I am Abominable.

By his fourth dosage, Crowley had decided to take desperate measures. When Sam pulled away with the syringe, the demon lunged out, clamping his teeth down on the hunter's fore arm and tearing the flesh, earning him a punch in the face and an exasperated Winchester. While the injured dressed his wound, the demon called for help, for _anyone_ who would hear him. When it came time for the next dosage, Sam returned in gauze completely unaware of his call. 

"How we doing moose?" Crowley chuckled, voice horse, as he kept his eyes locked on the table. "Ain't it about time for the next love inject- _shune_?" He then began to sing through the chorus of David Bowie's _Changes_ , but before he could finish the church began to shake. 

Sam's eyes began to dart around wildly, Crowley's as far as he could see, then focused as the wooden flooring began to crack and splinter, running up to break the demon trap. The rumbling continued as Crowley felt the slight release of his powers, he turned to the hunter. 

"Did you really think you could _kidnap_ the _**King of Hell**_ and _no one_ was gonna notice, dumb nuts?!" The church doors swung open to a familiar figure who strutted into ritual with a sway of her hips and a grin on her lips. 

"Hello boys." 

Crowley straightened, turning to her slightly. "That's my line." She quirked a brow out of sight and he continued. "Abbadon? They told me you were dead." 

"So not." 

The King shrugged. "And the rest of the cavalry?" 

"Oh no, it's just little, old, unkillable me." 

Sam turned quickly to the table and picked up a pistol, Abbadon throwing him against the wall as it went off and ricochet elsewhere. 

"Brilliant. Why send in a few grunts when you can send in a knight?" Crowley grinned to the Winchester as he tried to pick himself off the floor. "Say your prayers, moose!" He stood for only a second before with another flick of the wrist, Abbadon had sent him out the window. 

"That'll do." Crowley nodded, raising his wrists. "Undo these. I'll kill him myself." He sat back with a content sigh, waiting until he noticed her padding around to face him leisurely. 

"That was an _order_ , was it?" She asked, not making any movement to follow it through. Crowley knitted his brows together. "I am your _King_." He reminded her. 

"About that," 

Before he could blink, a solid fist collided with the King's face, causing him to jolt in his chair. He was getting weaker. He looked up to make a brash comment only to be greeted by her fist once, twice more. 

"Do you know I find the most shocking about time-traveling through a closet and landing in the year 2013?" Again she swung, and again and again, until Crowley was bleeding profusely from various part of his face and finally she managed to knock the chair over entirely. The King it the floor with an agonized groan, unable to defend himself in chains. She glanced to him queerly and continued. "Somebody thought it was a good idea to make you the King of Hell." 

Letting out strained gasps of breath, Crowley searched over the floor, looking for a way out. He noticed Sam's gun not far from him, maybe in reach. He needed to buy time. "You know what that boy's trying to do, right?" Abbadon's expression mimicked surprise as she began walking around him, noticing his feeble attempts to reach the pistol. "He's trying to shut the gates of Hell." Crowley looked up and saw her there, watching him as he became so close. She raised her hand and slid the gun across the floor, crushing all hopes as she knelt beside him. 

"Right now, you and I are going to talk about a regime change." 

Crowley turned painfully to stare at her fully. She was trying to take _his throne_? "You little whore." He glowered through his wounds and lifted himself from the ground slightly, raising his voice. " **I AM YOUR K-** " 

A swift boot knocked the word from his mouth, dazing him completely for several moments. Abbodon strutted around him, content with her work. She turned from him and was greeted instantly by a cool shower of gasoline and a Winchester holding a lit book of matches. 

"Love the suit."He commented, throwing the flames to her feet and setting her ablaze. 

Crowley could only just hear her muffled screams through the ringing in his ears. He was nearly blinded by the bright light of the flames flailing around him, he raised him arms, trying to block it out slightly as he watched her burn. She struggled for a bit but before she could be killed, she smoked out of the vessel, a black cloud running around the church and through the broken window with a shrill cry. When the silence took over, the remaining demon turned slightly meeting Sam's gaze. The Winchester approached him steadily and hoisted the chair, seating him upright with a groan and a sigh. 

"You did good back there, moose." Crowley said genuinely, happy to have the hunter back in control of things. "I'll deny it if you ever quote me, but I'm a proud man. I'm proud of you." 

Sam noted mentally that phrase sounded like something Bobby would have him say, but disregarded it as he gave a "Thanks." and rattled the spray can. 

"Hold on," The King's edginess returned, watching carefully as the Winchester walked behind him. "Uh, W-what's that?" 

"It's what it looks like." Sam assured, spraying the gap Abbadon had left in the trap. 

"Are you joking?" Crowley turned back his head as far as he could. "I just saved your life." 

Sam chuckled. "Seriously?" 

"Seriously? _Me_ , seriously?" The demon sputtered, his voice breaking. "We just shared a fox hole, you and I. We beat back the tet offensive, out run the- the rape of nanking, together! And you're still gonna do me like this?!" 

He recieved his answer in the form of a syringe being forced painfully into his neck, causing him to call out. When it was removed, he tried again. 

" _'Band of Brothers'? 'The Pacific'?_ None of this means anything to you? All those motels, you never once watched HBO, not _once_? _'Girls'_?" Sam turned to him incredulity. "You're my Marnie, moose. A-And Hannah, she just-, she _needs_ to be loved. She deserves it. Don't we all? You, me- we deserve to be loved. I _**deserve**_ , **TO BE LOVED!** " He took a breath, shakily, "... I just want to be loved." 

"... _What?_ " 

_Holy_ _**Fuck.**_

"...What?" Crowley repeated back calmly, looking confused as he began panicking internally. 

**WHAT IN THE FUCKING _HELL_ JUST HAPPENED?!** He had just had a complete bloody HBO-induced psychotic breakdown in front of moose, that's what just happened! He was becoming too mortal, and far too fast! God, one step further and Bobby would have been flying out of his mouth like smoke, for Christ's sake! _**How**_ was this happening to him?! Where did this humanity come from when he had none to begin with?! How was he feeling, all this fear, pain, grief, guilt? Oh _**God**_ , there was so much guilt. 

Everything he had ever done, as a human or demon, had hurt someone. His family, demons, humans, angels, the Winchesters- and he didn't care! He hadn't cared at all about any of them, and odds are he wouldn't have given a shit about them now if he wasn't so overwhelmed with guilt about Bobby. _Oh Bobby_ , how had he had the possession to leave him **_alone_** in Hell? At the very least, he could have popped him a warning, but that seemed too difficult a task at the time apparently, because he had just left the hunter there. He had hurt him, _God_ he had hurt him so much and he was _so sorry_. He was endlessly sorry and he would never be able to get to tell Bobby. 

Crowley had lost track of time in his thoughts as he glanced up the the Winchester, preparing himself. He bit his tongue unnerved, and cast his eyes to the floor. "...Would it be possible, moose,..." No, he had to correct himself. "I'd like,... to ask you a-a favor, _Sam_." He looked to the Winchester, now intrigued by his request. "Earlier... when, you were confessing, back there,... what did you say?" Sam gave him a suspicious look and remained silent. "I only ask because, given... my _history_ ,... it raises the question..." He paused, as if trying to figure it out himself. "Where... do I start... to even _**look**_ for forgiveness? I mean..." He trailed off. 

Sam began to raise his hand in an answer. "How about we start with this?" He asked, his blood filling the needle in his grip. 

Crowley looked to it, his eyes lined slightly with tears he didn't know he was capable of having, and finally gave in to the Winchester's plan. 

He tilted his head.


	12. Strike 3, You're Out

**THWACK**

The vamp's head flew off it's shoulders and down into the dirt, mouth still wide and baring pointed teeth. Bobby let the body fall after it, releasing it from the tree he had posted it to and letting the make-shift blade relax at his side. 

_Where in the Hell was Hell?_ He wasn't sure how long he had been searching, wandering through the endless woods of Purgatory or how many monsters he had faced along the way, but damn was Bobby feeling too old and dead for this. He just needed to find the portal. Three meeting trees covered by a rock shouldn't have been difficult, especially if he had crawled out of it, but this place seemed to be it's own _world_. It had no end in it's reaches and it had no limit to it's beasts. Millions upon millions of leviathans, vampires, werewolves, ghouls, _wendigos_ for crying out loud, all were on the hunt for him. 

When Ash had shown him the door, it was like that of an abandoned cabin; wood-rotted slightly, brittle and dry. The knob was chipped black, loosely attached as if it could fall off at any moment. 

"Now when you step through that door," Ash warned him, eyes shifting intently from the door to the older hunter. "It's a one way. There ain't any coming back." The idea of staying in heaven ran through Bobby's mind, but was stopped short by the thought of Crowley. _That damn demon._

"Thanks." He took a breath, reaching for the knob. 

"Wait." The mulleted man stopped him, pulling something from his belt. "If you're really goin' you'd better take this." He held out his arm, extending from it was the handle of an angel blade. Bobby was astounded and wanted to know where he had retrieved it, but he realized the story behind it was probably too much for him to want to hear. 

He nodded an appreciation and took it, attaching it to his belt, then opened the door. A rush of wind starting to suck in the loose papers around them, whistling as it started to pull him into the vortex. He looked to Ash one final time and stepped through it. 

Now he was here. Miles into his ungodly trek with no signs of ever being able to find the door back to Hell. 

There was a rustle somewhere behind him and the hunter turned, blade in hand, eyes locking onto the source then pausing in confusion. 

"Hello Bobby." The figure greeted him. He was well dressed and utterly lacking in the blood, dirt, and sweat of Purgatory. His blonde hair was swept perfectly to one side and brought out the pale blue-ness in his eyes. He made no movement to attack or lash out at the hunter, and there was no visible sign of wanting to on his content face, but his hands were behind his back, out of sight, and that was all Bobby needed to know. 

"Who are you and what the Hell do you want?" He spat in disdain. 

"My name is Malachi and I have been following you since heaven." 

"Well thanks for all the help." The hunter glared at the angel, who gave no sign of apology. 

"I could not my presence known. Had I, more beasts would have come for you and I. I had to wait until you had made it far enough out to be out for reach for a few moments." As Malachi explained, he stepped closer. Bobby reacted souly on interests and grabbed for the angel blade, holding it in defense. "Please, there is no need for that." 

"Yeah, and I suppose you ain't carrying one?" 

The angel dropped the argument. "Why did you leave heaven Bobby?" 

Bobby stopped. Heaven had sent a search angel after him? To what, _bring him back? _"Because I've got some things I've got to do."__

 _ _" _Things?_ " __

__

"None of you're damn business." 

Malachi sighed and cast his eyes down, a gesture that reminded the hunter of Castiel. "You need to come back with me." 

"Yeah? Says who?" 

"God." The angle paused, in the silence he continued. "Souls aren't supposed to leave heaven. It's infinitely vast beyond human measure, so none are ever cast aside. You're an innocent, and you've already lived in the heaven we've designed for you." 

"Hell of a job with that." The hunter muttered sarcastically. Malachi ignored him. 

"If you leave it without a soul, the foundation of it will crumble and it will be destroyed. Bobby if you do not come with me now, you will not be able to return to heaven." 

At that the angel blade lowered a bit, the hunter's brows knitted together in thought. _This was it._ He couldn't return to earth, he couldn't find the doorway to Hell, and if he refused Malachi's offer, his heaven would be lost. All that he could have left, would be Purgatory. He would be left running, fighting, and struggling everyday and for what? To be reanimated into the same thing over and over again? Or to be wiped out entirely. Bobby wasn't too sure he wanted to find out about that. But this was only if he _couldn't_ find Hell. 

He could keep looking. He no longer needed to sleep or eat, and he knew every creature that could come at him. He knew how to kill every threat that opposed him, ex-human or not, and he could keep fighting, pushing, making it to Hell and eventually, finding Crowley. He just had to keep fighting. 

"Well then I guess you've got room for someone else." He replied, regripping the blade and keeping it focused on Malachi. 

The angel's shoulders dropped in vexation and he narrowed his eyes. "What is it with you humans? You and the Winchesters. We offer you everything you could ever ask for, we give you our father's plan, and you do everything in your power to go against it, killing demons and my brothers alike. All for _what_?" 

Bobby glared at him with equal strength. "So that we can live on _normally_ and not have to worry about what you winged idgits do. Like the Apocalypse, for starters." 

"It was the Winchester's duty to fulfill their destinies and become Michael and Lucifer's vessels." Malachi snapped, his voice becoming softer though still ferocious. "We were supposed to win, live in paradise and have our leader. Now, _everything_ is in chaos." 

"Guess you better go take care of that." The hunter responded, not losing his attitude. "If you ever come across Castiel, ask him to explain the whole ' _Free Will_ ' thing." The angel frowned at him dishearteningly and seeing no change departed with a flutter, leaving him utterly alone. 

This was it. Bobby had given up _everything_. He only had one chance left, one way out of Purgatory. He needed to find the portal. He needed to get out of the endless hunting and killing spree. He needed to find Hell. 

He needed to find Crowley.

__


	13. Wicked Game

All that was around him was darkness. He was cramped, uncomfortable, sweaty, dirty, grimy and all around displeased with the entire scenario. Sure, he's been in worse places than the trunk of an Impala before, but that did not help the fact he had been lying in the same curled position with duct tape over his mouth for almost two friggin' days. Once he had heard the squirrel's voice, though fairly muffled, asking for his response to something, but in the next moment there was the repetitive pounding on the lid that soon gave him a headache. 

In all the places in the world and Hell, how did he end up here? The very King of Hell itself locked by a devil's trap in the Winchester's trunk. He could only growl and maul over his own thoughts, switching whatever revenge-planning topics frequently back to discomfort with every crack and pothole Dean managed to hit in the road, he swore the damn hunter was doing it on purpose. It wasn't until a rest stop, the boys parked out at a little picnic area out in the middle of no where, that he finally heard the pair of them growing closer. There was a click, and an incredibly bright light he tried to blink away as he sun hit him. 

"Oh yeah," He heard, clear as a bell as the brothers came into focus. "He's the junk in my trunk." 

Crowley remained fairly stagnant despite his internal malcontent building, but it had seemed he had reached a point to where he simply didn't care anymore. 

"Don't worry, your Royal Ass-ness," Dean jeered down at him. "Only got about a eighty miles to go." 

The demon looked up to him in indignation only for a moment before the lid was snapped back down, and he was left for the joy ride once more. He knew very little of cars other than what he had seen in films, by _why_ in the name of all things human did they choose to ride in these things? 

With the typical speeding Dean pulled down the road, they arrived at the bunker in less than an hour's time. When he was released from the trunk, Sam had thrown a black tarp over his head as well as what he assumed to be head phones, considering he couldn't hear a bloody thing. He was given no instruction as to where he was going and nearly took a tumble down a flight of stairs he hadn't known of, luckily the moose was gracious enough to prevent that tragedy. It wasn't until he was completely bound again, shackles, cuffs, collar and all, that they removed the bag from his head and the tape from his mouth. 

He had only let out a slight cry of pain, followed by a simple ' _Hello_ ' before the squirrel's fist collided with his face, knocking him flat back against the chair and all the force smacking head on to his nose. For a moment he was utterly stunned. 

"Ah, never get tired of doing that." Dean sighed, stepping back as Sam stepped up with a pen and pad. 

Crowley coughed and let out a groan, trying to identify which of his facial muscles he still had feeling in, then looked around. "Homey," He commented, taking note of the weapons plastered in steel cases lining the walls around him and the devil's trap containing him on the floor. "Where did you get this fantastic little tree house?" 

"Alright, here's how it's gonna go," Moose ignored him. "You're giving us the name of every demon on earth and the people they're possessing." 

"Am I?" The King raised a brow unfazed. He shook his head slightly. "Doesn't sound like me." 

"I saw you break down, Crowley." At the reminder the demon inwardly winced but remained stagnant. "When I was trying to cure you, I know part of you was human again, maybe still is." 

"Blah Blah. Boo hoo. Done?" Crowley intervened, not wanting to step too far into the memory. "Good. 'Cause this is what I know: I'm not giving you anything." He hissed at the hunters, not intimidated by their scowls. "Why would I? You've got no leverage, darlings. You're not gonna close the gates of Hell because you didn't, You're not gonna kill me because you haven't. So what's left?" 

"We have a few ideas." Dean aired confidently. 

"Torture? Brilliant. Can't wait to see Sam in stilettos and a leather bustier. Really putting the S-A-M into S-&-M." The demon grinned, becoming a bit more cocky in his mind as there was now nothing that the Winchesters could do to hurt him. "Honestly, boys, what are you gonna do to me that I don't do to myself just for kicks every Friday night?" 

The brothers remained silent, a victorious smile laying easily on Crowley's lips. They glanced to each other with the slightest nod before they turned, saying nothing in explanation as they headed out of the room. 

"Have fun." Dean grinned in return as he shut the door, leaving the demon in confusion. 

The lights went out, leaving only the sound of retreating footsteps followed by another door, before Crowley let out an impressed hum, surprised by this no idea to simply do nothing. He was left completely alone. The darkness sounding him seemed almost vast as his eyes adjusted to catch up with the lack of light. He turned repetitively, trying to make out various shapes and figures in the black fog of nothingness. There was nothing he could see. Nothing to distract him. He was left utterly alone. 

_Well. This is fun._

After a few moments he started humming to himself, various tunes and artists he favored, ' _Can't Smile Without You_ ' by Barry Manilow he even sung quietly to himself, whistling the melody when needed only to hear it echo back to him a moment later. After that he simply made noises; pops, clicks, and any other sounds he could create using his tongue and teeth, not sure any of that would be useful ever. And finally he had resorted to making up mock conversations, speaking either to an imaginative figure or simply to himself, he always had a good response and didn't spare in wit or grace. It started off as simple things, like fan theories and relationships on HBO, then politics in Hell and how he ruled as well as what he wanted to change when he returned, then he started picking at himself. 

He started digging deep, though he knew he should've left alone. But he was so curious and so tangled about his long lost humanity he had recently found as Sam was curing him. Did he truly want forgiveness? Did he truly want love? What pieces of his humanity were even there to start with? As a human, he'd never thought twice about either. He made his deal for the idea of lust and power and he hadn't cared at all for his so-called family. He had never harbored any regret for anything he had done, so why now was he feeling so guilty? 

He knew Bobby was at the bloody heart of it all, but he was trying to get past that. What was it that was making him feel this way? What humanity did he have? Where did it begin? When did he start feeling emotions rather than hate, rage, and pride? When did all of his contracts meant to screw over all the pathetic humans who would take them become and act of benevolence? 

And like that, all his thoughts came to a halt. 

"Holy Mother of Sin," He muttered to himself. 

That was it. 

The very first time he ever changed up a contract to the gain of the counter party, was the very same contract he had put on Bobby's soul for Death's location. Though it wasn't part of the deal, he gave the hunter his ability to walk. That's what started it all. 

When he had done it, Bobby had looked so awe-stricken, so overjoyed to be to stand, the demon couldn't help the smallest trace of a grin that appeared on his face as the hunter hugged the boys. Even later when they were hunting him in hopes of returning it, he had allowed Bobby to keep his legs. That's when it all had began: His fascination with the hunter. 

It intrigued the demon the hunter could be so much different from himself yet so undenyingly similar at the same time. Their words were laced with sarcasm and annoyance, they both had a taste for whisky, never changed from a particular style of clothing they wore, and ran entire organizations seemingly single handedly. He ran intel for other hunters as Crowley set jobs for his demons. Bobby was the mirrored, more innocent and less pompous-classed, version of himself. 

Perhaps another reason he found the hunter to be so enticing was the fact he was much more entertaining than other persons he had met. Most people upon meeting a demon are so terrified Crowley could practically feel their hearts pounding. Bobby on the other hand had barely let him get a word out before he had shot him with a revolver, and only a few minutes later knocked him on his tender ass with a shot gun full of rock salt. And if that alone wasn't enough to fascinated him with, when he had actually convinced the hunter to deal, he had taken his mouth whole, forcing his tongue into the demon's mouth and give him a Hell of a kiss over one little soul. 

He then reflected to all the little deals he had made with Bobby in Hell, how each time it was with blunt heat without much elegance or finesse, but yet so overwhelming Crowley couldn't helped but by drawn further in by each one. The caring, the ecstasy, the _passion_ he had started to feel all when he had been swept away by this ornery drunk bastard. Those were the starting emotions, and how fantastic they were all on their own. But when he left Hell, damn it all, when he left, all of that had been stripped down into two more awful ones the demon couldn't cope with: Guilt and Fear. 

Not since he had last seen the hunter had he stopped feeling guilty. He didn't know how to apologize or if he was capable of it at all, but the very fact that he couldn't even attempt to try it anymore was agonizing. And now he was stricken with the fear he would never be able to. He would never be able to explain to Bobby why he had left or how he had made him felt. The first hunter in history to give a demon feelings. 

If they ever wanted to try again, easily the Winchesters could make him human. They'd kill Juliet, rescue some damsel, no doubt, and then they'd change him. And after living a short life running from demons, angels, and hunters, his new-found soul would be sent back to Hell, locked in and eternally tortured. He never wanted it to come this far. He never wanted to be here. He never wanted to be the Winchester's prisoner or to harbor such intense emotions about a hunter who's soul was now lost in the infinite white clouds of heaven. He never wanted to be stuck in the darkness, thinking and questioning everything about himself, all the decisions he had made and how whatever humanity he had was torn to shreds. He never wanted to feel so alone in the silence that he would give anything, _anything_ just to hear Bobby's voice, even it was just to scold him and call him infamously an idgit. 

All he wanted was to be loved. 

He never wanted to fall into it.

**Notes for the Chapter:**

> *****Update!!
> 
> I'm so so sorry I haven't been here to finish this story. Unfinished works are literally Satan's spawn. But I DO PROMISE I WILL FINISH THIS STORY. It's been difficult lately for me to work on this whilst moving and other mundane tasks, and I've been trying to finish up another story as well. I'm so sorry for the wait on all this, but for now and the better of us I'm going to put this story on hold. I won't take it down in the meantime so others can view it, but for right now (and I hope only to be brief) I will be inactive with this story. 
> 
> My sincerest apologies again for all this, but again, I WILL FINISH THIS STORY. I will go down with this bloody ship if it kills me.
> 
> ~RainiDayz


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